Dimethyl Sulfoxide → Benzyl 3-formylpyrrolidine-1-carboxylate

HRID 1524794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1524794
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14]1.O>C(Cl)Cl>[CH:12]([CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14]1)=[O:11]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 18332648Benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 4620242Benzyl 3-formylpyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

DMSO (597 μL, 8.42 mmol) was added to a solution of oxalyl chloride (427 μL, 5.05 mmol) in DCM (25 mL) at −78° C. After 5 minutes, benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (generated in Step 1) was added. The reaction was continued for 30 minutes at −78° C. TEA (2.3 mL, 17 mmol) was then added. The resulting mixture was then allowed to warm to room temperature over the course of 30 minutes. Water was then added. The layers were separated and the organic phase was washed sequentially with 0.1 N HCl, water, saturated NaHCO3, and brine. The organic phase was then dried over sodium sulfate and the solvent was removed in vacuo to afford the product (0.82 g, 88% over two steps).

Aufarbeitung

  1. waitThe reaction was continued for 30 minutes at −78° C
  2. customThe layers were separated
  3. washthe organic phase was washed sequentially with 0.1 N HCl, water, saturated NaHCO3, and brine
  4. dry with materialThe organic phase was then dried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customto afford the product (0.82 g, 88% over two steps)

Quellen und Nachweise

ORD-Eintrag
ord-1e4c4ee728c04f198fc5d76be975b735
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079912B2

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